Pirate Adventures on the Chesapeake

Pirate Adventures on the Chesapeake "On the pirate ship Sea Gypsy we always find the treasure, we always defeat that stinky pirate, and the children always walk away with incredible stories!"
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Sail away in search of sunken treasure aboard our children's pirate cruise in the Annapolis Harbor. Perfect for family fun, field trips and birthday parties Pirate Adventures is an interactive experience on the high seas. Fire our famous water cannons, face painting and dress up, and a treasure hunt on the water make for an unforgettable adventure that your kids will remember for years to come.

Wow! The weather forecast is the BEST is has been all summer, come out and seas the day with us! ⚓☀️
07/25/2026

Wow! The weather forecast is the BEST is has been all summer, come out and seas the day with us! ⚓☀️

07/20/2026

And we are sold out - thank you to everyone that waited in line - on the fun part!!!

21 tickets left at 3:30 pm come on down and get them! $5 ONE DAY ONLY.
07/20/2026

21 tickets left at 3:30 pm come on down and get them! $5 ONE DAY ONLY.

07/18/2026

$5 DAY HAPPENS ON 7/20

🏴‍☠️ 5 DAY INFORMATION 🏴‍☠️

🎟️ You cannot make a reservation for $5 Day, you must come purchase the tickets in person.

📍 The line will form at our location: 311 Third St. Annapolis, MD 21403. There will be signage indicating where to form the line.

⏰ The door will open promptly at 8am

🚢 There are 45 tickets available on six sailing time at 9:30, 11:00, 12:30, 2:00, 3:30, and 5:00

🎫 A total of 270 tickets are available for the day

👶 Every person, regardless of age, even an infant does need a ticket on the boat.

💰 There is not a limit on the amount tickets one person can purchase. Early bird gets the treasure!

⚓ We will sell all the tickets on a sailing (9:30 first) before the next boat becomes available.

❌ Once we have sold all 270 tickets for the six trips we will be sold out for the day. $5 tickets are only available on Monday, July 20th, 2026.

🌧️ Tickets are non-refundable unless Pirate Adventures makes the decision to cancel in the event of any steady rain, thunderstorms, or high winds. If we need to cancel the trip your tickets will be refunded when you arrive for your scheduled trip.

⏳ Tickets will be sold to standby passengers if you do not show for your trip or do not use all the tickets purchased.

☎️ We hope to see you on $5 day! If you have any questions about how $5 works please don’t hesitate to give us a call at (410) 263-0002.

Address

311 Third Street
Annapolis, MD
21403

Opening Hours

Monday 8:30am - 6:30pm
Tuesday 8:30am - 6:30pm
Wednesday 8:30am - 6:30pm
Thursday 8:30am - 6:30pm
Friday 8:30am - 6:30pm
Saturday 8:30am - 6:30pm
Sunday 8:30am - 6:30pm

Telephone

+14102630002

Website

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